Akuammine
Title: Akuammine
CAS Registry Number: 3512-87-6
Additional Names: Vincamajoridine
Molecular Formula: C22H26N2O4
Molecular Weight: 382.45
Percent Composition: C 69.09%, H 6.85%, N 7.32%, O 16.73%
Literature References: From seeds of Picralima nitida (Stapf.) Th. & H. Dur. (P. klaineana Pierre), Apocynaceae: T. A. Henry, T. M. Sharp, J. Chem. Soc. 131, 1950 (1927); T. A. Henry, ibid. 1932, 2759. Identity with vincamajoridine from Vinca major L., Apocynaceae: M. M. Janot et al., Experientia 11, 343 (1955). Structure and chemistry: M. F. Millson et al., ibid. 9, 89 (1953); Saxton, Q. Rev. Chem. Soc. 10, 141 (1956); J. A. Joule, G. F. Smith, J. Chem. Soc. 1962, 312. Revised structure and absolute configuration: L. Olivier et al., Bull. Soc. Chim. Fr. 1965, 868.
Properties: Crystals, decomp 255°. [a]D16 -105.3° (c = 1.31 in pyridine). pKa 7.5. uv max (ethanol): 245, 312 nm (log e 3.96, 3.66). Slightly sol in water, cold alcohol; sol in boiling alcohol, chloroform, acetone.
pKa: pKa 7.5
Optical Rotation: [a]D16 -105.3° (c = 1.31 in pyridine)
Absorption maximum: uv max (ethanol): 245, 312 nm (log e 3.96, 3.66)
 
Derivative Type: Hydrochloride ethanolate
Molecular Formula: C22H26N2O4.HCl.C2H5OH
Molecular Weight: 464.98
Percent Composition: C 61.99%, H 7.15%, N 6.02%, O 17.20%, Cl 7.62%
Properties: Crystals, mp 232-233°.
Melting point: mp 232-233°
 
Derivative Type: Methyl ether
Molecular Formula: C23H28N2O4
Molecular Weight: 396.48
Percent Composition: C 69.67%, H 7.12%, N 7.07%, O 16.14%
Properties: Needles from acetone, mp 242-243°. uv max (ethanol): 244, 308 nm (e 11500, 4200).
Melting point: mp 242-243°
Absorption maximum: uv max (ethanol): 244, 308 nm (e 11500, 4200)
 
 
Status: This monograph has been retired and is no longer subject to revision or update.

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